Meat Loaf
Meat Loaf was a major success story in the '70s when he released Rocky Horror Picture Show and Bat Out of Hell, but he fell into a financial hole in 1983 and was forced to file bankruptcy. He got caught up in 45 lawsuits, all from major companies, which drained his bank account and crushed his morale. He started to come back a bit in the '90s, but he was ultimately unable to recoup his losses.